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Chapter 4: Problem 64

Write expanded structures showing the \(\mathrm{C}-\mathrm{C}\) bonds for each of the following condensed formulas. Name each substance by an accepted system. a. \(\left(\mathrm{CH}_{2}\right)_{10}\) (saturated compound only) b. \(\left(\mathrm{CH}_{2}\right)_{5} \mathrm{CHCH}_{3}\) (c) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{C}\left(\mathrm{CH}_{2}\right)_{6} \mathrm{CHC}_{2} \mathrm{H}_{5}\) d. The isomers of trimethylcyclobutane e. \(\left(\mathrm{CH}_{2}\right)_{6} \mathrm{CHCH}_{2} \mathrm{C}\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CH}_{2} \mathrm{CI}\) f. \(\left[\left(\mathrm{CH}_{2}\right)_{2} \mathrm{CH}\right]_{2} \mathrm{C}\left(\mathrm{CH}_{3}\right) \mathrm{C}_{2} \mathrm{H}_{5}\)

Short Answer

Expert verified
a. Expanded Structure: \( \mathrm{CH}_{3}\mathrm{CH}_{2}\mathrm{CH}_{2}\mathrm{CH}_{2}\mathrm{CH}_{2}\mathrm{CH}_{2}\mathrm{CH}_{2}\mathrm{CH}_{2}\mathrm{CH}_{2}\mathrm{CH}_{3}\); IUPAC Name: decane. b. Expanded Structure: \( \mathrm{CH}_{3}\mathrm{CH}_{2}\mathrm{CH}_{2}\mathrm{CH}_{2}\mathrm{CH}_{2}\mathrm{CH}_{2}\mathrm{CH}= \mathrm{CH}\mathrm{CH}_{3}\); IUPAC Name: 7-methyl-1-heptene. c. Expanded Structure: \( \mathrm{CH}_{3}\mathrm{C}(\mathrm{CH}_{3})\mathrm{CH}_{2}\mathrm{CH}_{2}\mathrm{CH}_{2}\mathrm{CH}_{2}\mathrm{CH}_{2}\mathrm{CH}_{2}\mathrm{CH}= \mathrm{CH}\mathrm{CH}_{2}\mathrm{CH}_{3}\); IUPAC Name: 2,2-dimethyl-7-octene. d. Isomers of trimethylcyclobutane: 1,1,2-trimethylcyclobutane and 1,2,3-trimethylcyclobutane. e. Expanded Structure: \( \mathrm{CH}_{3}\mathrm{CH}_{2}\mathrm{CH}_{2}\mathrm{CH}_{2}\mathrm{CH}_{2}\mathrm{CH}_{2}\mathrm{CH}= \mathrm{CH}\mathrm{C}(\mathrm{CH}_{3})_{2}\mathrm{CH}_{2}\mathrm{CH}_{2}\mathrm{Cl\); IUPAC Name: 9-chloro-2,7,7-trimethylnon-6-ene. f. Expanded Structure: \( \mathrm{CH}_{3}\mathrm{CH}_{2}\mathrm{C}(\mathrm{CH}_{2}\mathrm{CH}_{3})\mathrm{C}(\mathrm{CH}_{2}\mathrm{CH}_{3})\mathrm(CH_{3})\); IUPAC Name: 2,2-bis(propan-2-yl)-1-ethyl-1-methylpropane.

Step by step solution

01

Draw the expanded structure

Since it's a saturated compound, there are ten carbon atoms connected in a single chain with single bonds (No double or triple bonds). \( \mathrm{CH}_{3}\mathrm{CH}_{2}\mathrm{CH}_{2}\mathrm{CH}_{2}\mathrm{CH}_{2}\mathrm{CH}_{2}\mathrm{CH}_{2}\mathrm{CH}_{2}\mathrm{CH}_{2}\mathrm{CH}_{3}\)
02

Name the substance using IUPAC nomenclature

The name for the given compound is decane. b. \(\left(\mathrm{CH}_{2}\right)_{5} \mathrm{CHCH}_{3}\)
03

Draw the expanded structure

There are five carbon atoms connected with single bond followed by a carbon atom double bonded to another carbon atom which is bonded to a methyl group. \( \mathrm{CH}_{3}\mathrm{CH}_{2}\mathrm{CH}_{2}\mathrm{CH}_{2}\mathrm{CH}_{2}\mathrm{CH}_{2}\mathrm{CH}= \mathrm{CH}\mathrm{CH}_{3}\)
04

Name the substance using IUPAC nomenclature

The name for the given compound is 7-methyl-1-heptene. c. \(\left(\mathrm{CH}_{3}\right)_{2}\mathrm{C}\left(\mathrm{CH}_{2}\right)_{6} \mathrm{CHC}_{2} \mathrm{H}_{5}\)
05

Draw the expanded structure

Two methyl groups are bonded to one carbon atom, followed by six carbon atoms connected in a single chain. The next carbon is double bonded to another carbon, which has an ethyl group. \( \mathrm{CH}_{3}\mathrm{C}(\mathrm{CH}_{3})\mathrm{CH}_{2}\mathrm{CH}_{2}\mathrm{CH}_{2}\mathrm{CH}_{2}\mathrm{CH}_{2}\mathrm{CH}_{2}\mathrm{CH}= \mathrm{CH}\mathrm{CH}_{2}\mathrm{CH}_{3}\)
06

Name the substance using IUPAC nomenclature

The name for the given compound is 2,2-dimethyl-7-octene. d. The isomers of trimethylcyclobutane
07

Draw the expanded structures for isomers

Two possible isomeric structures for trimethylcyclobutane are: 1,1,2-trimethylcyclobutane: ![1,1,2-trimethylcyclobutane](https://www.daylight.com/dayhtml/doc/theory/theory27.gif) 1,2,3-trimethylcyclobutane: ![1,2,3-trimethylcyclobutane](http://www.orgsyn.org/demo.aspx?prep=cv5p0942) e. \(\left(\mathrm{CH}_{2}\right)_{6} \mathrm{CHCH}_{2}\mathrm{C}\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CH}_{2} \mathrm{CI}\)
08

Draw the expanded structure

There are six carbon atoms connected in a single chain, followed by a carbon double bonded to another carbon, which is further bonded to two methyl groups and chloroethyl group. \( \mathrm{CH}_{3}\mathrm{CH}_{2}\mathrm{CH}_{2}\mathrm{CH}_{2}\mathrm{CH}_{2}\mathrm{CH}_{2}\mathrm{CH}= \mathrm{CH}\mathrm{C}(\mathrm{CH}_{3})_{2}\mathrm{CH}_{2}\mathrm{CH}_{2}\mathrm{Cl}\)
09

Name the substance using IUPAC nomenclature

The name for the given compound is 9-chloro-2,7,7-trimethylnon-6-ene. f. \(\left[\left(\mathrm{CH}_{2}\right)_{2} \mathrm{CH}\right]_{2}\mathrm{C}\left(\mathrm{CH}_{3}\right) \mathrm{C}_{2} \mathrm{H}_{5}\)
10

Draw the expanded structure

Two propylene groups are bonded to a central carbon atom, which is further bonded to a methyl and ethyl group. \( \mathrm{CH}_{3}\mathrm{CH}_{2}\mathrm{C}(\mathrm{CH}_{2}\mathrm{CH}_{3})\mathrm{C}(\mathrm{CH}_{2}\mathrm{CH}_{3})\mathrm(CH_{3})\)
11

Name the substance using IUPAC nomenclature

The name for the given compound is 2,2-bis(propan-2-yl)-1-ethyl-1-methylpropane.

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Most popular questions from this chapter

(a) trans-1, 2-Dimethylcyclohexane exists about \(99 \%\) in the diequatorial conformation; trans-1, 2-Dibromocyclohexane on the other hand, exists about equally in diequatorial and diaxial conformations. Furthermore, the fraction of the diaxial conformation decreases with increasing polarity of the solvent. How do you account for the contrast between the dimethyl and dibromo compounds? (b) If trans-3-cis-4-dibromo-tert-butylcyclohexane is subjected to prolonged heating, it is converted into an equilibrium mixture (about \(50: 50\) ) of itself and a diastereomer. What is the diastereomer likely to be? How do you account for the approximately equal stability of these two diastereomers? [Here, and in (c), consider the more stable conformation of each diastereomer to be the one with an equatorial tert-buty1 group]. (c) There, are two more diastereomeric 3,4 -dibromo tert-butylcyclohexanes. What are they? How do you account for the fact that neither is present to an appreciable extent in the equilibrium mixture?

Investigate the thermodynamic feasibility of the following propagation steps for opening the rings of cycloalkanes with \(\mathrm{n}=2-6 \mathrm{by}\) a free-radical mechanism. (1) \(\left(\mathrm{CH}_{2}\right)_{\mathrm{n}}+\mathrm{Br}^{-} \rightarrow \mathrm{BrCH}_{2}\left(\mathrm{CH}_{2}+\mathrm{n}-2 \mathrm{CH}_{2}\right.\) (2) \(\mathrm{BrCH}_{2}\left(\mathrm{CH}_{2}+\mathrm{n}-2 \mathrm{CH}_{2}+\mathrm{Br}_{2} \rightarrow\left(\mathrm{CH}_{2}\right)_{\mathrm{n}-2}\left(\mathrm{CH}_{2} \mathrm{Br}\right)_{2}+\mathrm{Br}^{-}\right.\) Use 83 kcal for the bond-dissociation energy of a normal C-C bond and \(68 \mathrm{kcal}\) for the bond-dissociation energy of a C-Br bond. (An easy way to solve a problem of this type is to first calculate AH of each step for cyclohexane where there is no strain, and then make suitable corrections for the strain which is present for small values of n.) Refer to the following table for your answer. Table 1. Total Strain of Cycloalkanes $$ \begin{array}{|c|c|c|} \hline \begin{array}{c} \text { Cycloalkane } \\ \left(\mathrm{CH}_{2}\right)_{\mathrm{n}} \end{array} & \mathrm{n} & \begin{array}{c} \text { Total strain } \\ (\mathrm{kcal} / \text { moles }) \end{array} \\ \hline \text { ethylene } & 2 & 22.4 \\ \hline \text { cyclopropane } & 3 & 27.6 \\ \hline \text { cyclobutane } & 4 & 26.4 \\ \hline \text { cyclopentane } & 5 & 6.5 \\ \hline \text { cyclohexane } & 6 & 0.0 \\ \hline \end{array} $$

Which of the following compounds are resolvable, and which are non-resolvable? Which are truly meso compounds? Use models as well as drawings. (d) tran-1, 2-cyclohexanediol (a) cis-1,2-cyclohexanediol (b) trans-1,2-cyclohexanediol (e) cis-1,4-cyclohexanediol (c) cis-1,3-cyclohexanediol (f) trans-1,4-cyclohexanediol

You have two bottles labeled "1, 2-Cyclopentanediol," one containing a compound of m.p. \(30^{\circ}\), the other a compound of m.p. \(55^{\circ}\); both compounds are optically inactive. How could you decide, beyond any doubt, which bottle should be labeled "cis" and which "trans"?

There are two isomers of decalin. One is of higher energy and the other is more stable. Which is the stabler form? Why?
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